One thing that I hate about it is, if a notification pops up and you are on a different screen or in a different app, when you mouse over the notification to click it to go away, rather than sending the notification away, it sends it to the background and brings outlook to the front.

So you then have to minimize outlook or move it out of the way to get to the notification screen to close the notification screen.

Also it continuously disables extensions because it's so fucking prioritized on minimizing boot-up time that it does not give a single fuck about how much extra time you have to waste re-enabling the goddamn extensions that you need in order to do your job.

We're paying good money for these extensions.

We want them.

We don't care about 1.3 fucking seconds of time it takes for Outlook to start up as long as we have the functionality, and Microsoft's Outlook keeps disabling them.

If this were a single computer, it would be a hassle. But this is company-wide, having to constantly train and go over how to re-enable the extensions that we need to keep enabled in order for our employees to do their fucking job that we're paying Microsoft $25 a month per person for.

or how about how Microsoft forces, Microsoft accounts to be created, but won't allow Microsoft accounts to be created using organization credentials.

But then it goes behind your back and creates a Microsoft account for every single organization credential.

And then it hides that from you inside of Edge so that you first have to remove the organization credential from Edge and then do a search and then remove the organization credential from being inside of Edge just to stop Edge from having an organization credential that it uses to track every single user in your organization and every single thing that they do.

So yeah, fuck Microsoft.

Adding a group. You can now only add one email address at a time. Got a group of 100? Best clear your afternoon.

Not being able to unpin email chains unless you change it to non-threaded replies, select all, unpin, then go back to threaded replies like a civilized lifeform. Otherwise it just repins the chain when it refreshes.

Our office also uses teams phones which still don't have a way to show missed calls. We literally cannot call people back if we don't get to the med room phone in time.

Setting up calendar events with reminders that never happen. At some point, they just stopped working for me.

My inbox view gets messed up every now and then and I have to keep resetting it.

The new version written in JavaScript and spite. Everything about that.

It's made by raccoons that live in a PCP factory dumpster. Also why the fuck do we need 4 different teams applications

Fuck Microsoft.

When you try to change views in a shared calendar, and it automatically switches to your personal calendar in the other view, causing you to go back to the first view, change calendars, then do the exact same thing again.

Every. Damn. Time.

Also cached exchange mode is a disaster...

When you have the calendar open it refreshes and blinks while it does that, like every 15 minutes. This never happened with 2016

And people pay through the nose for that crap?

There's a keyboard shortcut to send an email.

Having to use Outlook was a significant contributor to me leaving my last job.

I resend a lot of email. Reply all, update subject, screenshots etc. A few seconds after you reply all, above the to field you start getting status updates. You're not replying to the latest email. This will be sent to xx people etc. It shifts all the fields down, so my click into the subject to remove the RE: is now editing the cc field instead.

Are we talking about Outlook or "New Outlook"? Everyone that I've heard that switch to new Outlook has had nothing but pain that you can't "do the thing" you used to any more. Like "Meeting with All".

Jesus. Basically everything about it. We use the web client at work, so might be a different set of annoyances.
deep breath I use slashes in 70% of the e-mails I write as the punctuation mark that they are - I have never and will never want it to start randomly guessing what files I want to attach to the e-mail when I type a slash.
I actually didn't hate that if you typed something like "23rd" it would make the rd super-script - until the day it started doing it so incredibly wrong that it would super-script the '3' and the 'r' and change the 'd' to a 'th' so it read "2^3r^th".
Several times per day it will show a folder name in bold with a number in parenthesis telling me I have new messages in that folder, but when I click on the folder it highlights nothing as new messages, so I have to just remember what the last message I actually read was. Search sucks. Rarely can I open attachments. I told a coworker just yesterday that if they want to keep something secret from me, their best bet is to put the secret in an e-mail attachment and e-mail it to me.

I started using Outlook365 in browser during the pandemic, and never switched back. Not that much better, but I prefer the web app running in Firefox to the actual program.

Plus, at this point, if I even opened Outlook proper, Windows would probably freeze while trying to index all of the emails that have come and gone since the last time I opened it.

Idk why MS lets you use add-ins but then they go and disable it if it starts misbehaving according to Microsoft's determination of it doing so and not the actual add-in causing problems. OH—and then guess what? You can't fucking enable every add-in. For some, you can only tell Outlook to not disable it for a month and then it's the same thing all over again. Fucking Microsoft!

EDIT:

Also, who is the bird brain that decided it was a good idea to force add-ins to be managed partially via the browser? Like if I click one of the manage Add-in buttons in the Outlook app, it works just in Outlook but the other one opens up browser.

Also also, why tf are there 2 different Outlook apps now? Why should an image have Outlook New and Outlook Classic? Why tf does the mail app even exist at this point?

I have two instances open for two different inboxes and try to pull one up on the taskbar, the wrong instance will pull up every single time without fail.

That sounds like how everyone always guesses wrong which way to plug in USB, not a specific problem with outlook.

Labels should be the default but UI designers on all platforms only care about appearance. Googling says you can change the taskbar to not combine instances and show labels. That way you always know what you are clicking.

On the new Outlook, clicking on emails that pop up opens them... in the background. Insane design choice

For some reason, opening attachments is a lot more painful that it needs to be in open emails.

Maybe there is an option to remove "open file in browser" but if there is I haven't found it. Awful, awful design

When I click in the search-box in the titlebar, Outlook freezes for about 5 seconds.

You can't cut and paste an appointment.

I tried making a template the other day. I was successful, but it's multiple clicks whenever I want to use it. There's no way to customize the ribbon and add a button to use my new template.